Documentation Platform Engineer
Tailscale · Remote (United States)
About this role
**Documentation Platform Engineer — Tailscale** Thanks for considering Tailscale! If this role resonates with you, we encourage you to apply. **About Tailscale** Tailscale makes safe connections effortless by delivering software that helps you securely interconnect people and their devices—no matter where they are. Teams use Tailscale to protect networks, share access to internal tools, and more. Founded in 2019 and fully distributed, we’re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. --- ## About the Role We’re looking for an experienced **full-stack Documentation Platform Engineer** to evolve our [documentation](https://tailscale.com/docs) site into a platform that delivers an exceptional experience for prospective and current customers. You’ll build, maintain, evolve, and support the platform and tools internal teams and external contributors use to showcase Tailscale’s features and products—covering the documentation platform itself, content pipelines, API documentation, and search. This is a highly visible, customer-facing role where you’ll influence how documentation is created, published, and consumed. --- ## Key Responsibilities - Continuously improve and evolve our documentation site to create a helpful, delightful, educational experience for homelabbers, developers, and enterprises (and their agents). - Maintain and expand docs-as-code tooling and content publishing pipelines to enable internal and external contributors to publish error-free content quickly. - Work cross-functionally with engineering and product teams to integrate documentation with the Tailscale platform. - Partner with designers, user research, and growth teams to implement designs and features from experimentation to production. - Help shape and tune modern search and discovery infrastructure so visitors and agents can find answers quickly. - Collaborate with open source contributors via GitHub discussions, issues, and pull requests. - Monitor platform performance and maintain scalability for millions of visitors per month. - Stay ahead of documentation trends through research, experimentation, and measuring results. --- ## What We Are Looking For - Proven experience building, extending, maintaining, and deploying documentation sites using tools like **Hugo** or **Docusaurus**, or documentation platforms built on **NextJS**, **Astro**, or similar. - Familiarity with **docs-as-code** publication workflows and an understanding of how documentation quality impacts awareness, adoption, and growth. - Fluency in **TypeScript/JavaScript** and **React**; comfortable with **Python**, **CLI tools**, **shell scripting**, and **Git**. - Comfort with modern **HTML/CSS** and the ability to implement designs provided by others. - Experience with **CI/CD**, automated testing, and automation for content/documentation workflows to reduce repetitive tasks and provide real-time feedback to authors. - Ability to explain the impact and implications of **LLMs** both as tools for application development and as consumers of documentation content. --- ## Nice to Have - Open source experience and comfort engaging with contributors on GitHub issues and pull requests. - Understanding of how LLMs consume and interact with documentation. - Understanding multi-format content output (HTML, JSON, XML, raw Markdown, PDF, ePub). --- ## What We Offer - **Inclusive, flexible environment** where you can be your authentic self. - **Competitive total compensation** (ba
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